CN109641872B - 3-pyridyloxyphenyldihydrouracil compounds and use thereof - Google Patents
3-pyridyloxyphenyldihydrouracil compounds and use thereof Download PDFInfo
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- CN109641872B CN109641872B CN201780051327.3A CN201780051327A CN109641872B CN 109641872 B CN109641872 B CN 109641872B CN 201780051327 A CN201780051327 A CN 201780051327A CN 109641872 B CN109641872 B CN 109641872B
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- 230000002378 acidificating effect Effects 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
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- 150000001408 amides Chemical class 0.000 description 1
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- 201000000053 blastoma Diseases 0.000 description 1
- CURLHBZYTFVCRG-UHFFFAOYSA-N butan-2-yl n-(3-chlorophenyl)carbamate Chemical compound CCC(C)OC(=O)NC1=CC=CC(Cl)=C1 CURLHBZYTFVCRG-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
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- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
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- 229920000159 gelatin Polymers 0.000 description 1
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
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- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
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- 230000001404 mediated effect Effects 0.000 description 1
- LINPVWIEWJTEEJ-UHFFFAOYSA-N methyl 2-chloro-9-hydroxyfluorene-9-carboxylate Chemical compound C1=C(Cl)C=C2C(C(=O)OC)(O)C3=CC=CC=C3C2=C1 LINPVWIEWJTEEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002420 orchard Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Chemical class 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229960004029 silicic acid Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention provides a compound represented by formula (1) which has excellent controlling efficacy against plant diseases and is useful as an active ingredient of a plant disease controlling agent.
Description
Technical Field
This patent application claims priority and benefit under the paris convention based on japanese patent application 2016-.
The present invention relates to 3-pyridyloxyphenyl dihydrouracil compounds and their use.
Background
Hitherto, various compounds for controlling plant diseases have been developed and used for practical applications.
Documents of the prior art
Non-patent document
Non-patent document 1: the Pesticide Manual, 16 th edition (BCPC published) ISBN 978-1-901396-86-7.
Summary of The Invention
Problems to be solved by the invention
The present invention addresses the problem of providing a compound having excellent control efficacy against plant diseases.
Means for solving the problems
The present inventors have conducted studies to find a compound having an excellent controlling effect on plant diseases, and as a result, found that a compound represented by the following formula (1) has an excellent controlling effect on plant diseases.
That is, the present invention is as follows.
[1] A compound represented by the formula (1) (hereinafter referred to as the compound of the present invention):
[ chemical formula 1]
[2] A plant disease control agent comprising the compound described in [1] (hereinafter also referred to as the present invention control agent).
[3] A method for controlling a plant disease by treating a plant or soil in which a plant is cultivated with an effective amount of the compound according to [1 ].
[4] [1] use of the compound described in [1] for controlling plant diseases.
Effects of the invention
The invention can prevent and treat plant diseases.
Modes for carrying out the invention
The control agent of the present invention is generally used by mixing the compound of the present invention with a solid carrier, a liquid carrier, an oil and/or a surfactant, etc., adding a formulation adjuvant such as a binder, a dispersant, a stabilizer, etc., as needed, and formulating into a wettable powder, a water-dispersible granule, a flowable agent, a granule, a dry flowable agent (ドライフロアブル), an emulsion, an aqueous liquid, an oil agent, a fumigant, an aerosol, a microcapsule, etc. These preparations contain the compounds of the invention in a proportion of usually 0.1 to 99% by weight, preferably 0.2 to 90% by weight.
Examples of the solid carrier include fine powders and particulates of clays (e.g., kaolin clay, diatomaceous earth, synthetic hydrous silica, Fubasami clay, bentonite, and acid clay), talc, and other inorganic minerals (e.g., sericite, quartz powder, sulfur powder, activated carbon, calcium carbonate, and hydrated silica).
Examples of the liquid carrier include water, alcohols (methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (toluene, xylene, ethylbenzene, methyl naphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl ether, etc.), amides (dimethylformamide, dimethylacetamide, etc.), and sulfoxides (dimethyl sulfoxide, etc.).
Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkylaryl ethers and polyoxyethylene compounds thereof, polyoxyethylene glycol ethers, polyol esters, and sugar alcohol derivatives.
Examples of the other formulation adjuvants include binders, dispersants, and stabilizers, and specifically, casein, gelatin, polysaccharides (e.g., starch, gum arabic, cellulose derivatives, and alginic acid), lignin derivatives, bentonite, saccharides, synthetic water-soluble polymers (e.g., polyvinyl alcohol, polyvinylpyrrolidone, and polyacrylic acids), PAP (acidic isopropyl phosphate), BHT (2, 6-di-tert-butyl-4-methylphenol), BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, and fatty acids.
Examples of the oil and surfactant that can be used in combination with the compound of the present invention include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), ihanol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), SundanceII (registered trademark), inductor (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (registered trademark), Emulgator NP7 (registered trademark), emulate (registered trademark), Triton X45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), ensray N (registered trademark), and BANOLE (registered trademark).
The compounds according to the invention are applied as the control agents according to the invention. The method of applying the control agent of the present invention is not particularly limited as long as the control agent of the present invention can be applied substantially, and examples thereof include treatment of plant bodies such as stem and leaf spreading, treatment of plant cultivation areas such as soil treatment, and treatment of seeds such as seed disinfection.
The treatment amount of the compound of the present invention in the control method of the present invention varies depending on: the compound of the present invention is used in the case of treating the stem and leaf of a plant or treating the soil in which a plant is cultivated, for example, the type of plant to be treated, the type and frequency of occurrence of plant diseases to be controlled, the form of a preparation, the treatment period, the treatment method, the treatment place, and the weather conditions, and is used in the case of treating the stem and leaf of a plant or treating the soil in which a plant is cultivated2Usually 1 to 500 g.
Emulsions, wettable powders, flowables, etc. are generally treated by dilution with water and dispersion. In this case, the concentration of the compound of the present invention is usually 0.0005 to 2% by weight. Powders, granules and the like are usually treated as they are without dilution.
The compound of the present invention can be used as a plant disease control agent in farmlands such as dry farmlands, paddy fields, grasslands, orchards, etc.
Examples of the plant diseases which can be controlled by the compound of the present invention include diseases derived from plant pathogenic fungi such as filamentous fungi and bacteria, and specifically include the following. The scientific name of the pathogen causing the disease is shown in parentheses.
Rice blast (Magnaporthe grisea), flax leaf spot (Cochliobolus miyabenus), sheath blight (Rhizoctonia solani), bakanae disease (Gibberella fujikuroi), and yellowing atrophy (Phytophthora grandis (Sclerophora)); powdery mildew of wheat (powdery mildew (Blumeragramis) of Gramineae), gibberellic disease (Fusarium graminearum), Fusarium avenaceum (Fusarium avenaceum), Fusarium graminearum (Fusarium culmorum), Microdochium nivale (Microdochium nivale)), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), red rust (Puccinia recondita), red snow rot (Microdochium nivale), Microdochium nivale (Microdochium majus), small snow rot sclerotinia (Tyllungiensis), black rot sclerotium (Tyllungiella nivea), black rot sclerotium (Tyllungiensis), loose wheat (Utilia), and black wheat (Utilia triticum) smus (Utilis), wheat scab (Utilis nivea), wheat (Utilis nivea)Tilletia graminis (Tilletia caries), Tilletia controversa (Tilletia controversa)), Ocular leaf spot (Pseudocercospora herpotrichoides), glume blight (Stagonospora nodorum), maculopathy (Helminthosporium nodorum), Xanthomonas leaf spot (Pyrenophora tritici-repentis), seedling blight (Rhizoctonia solani) caused by Rhizoctonia sp, and seedling blight (Rhizoctonia cerealis) (Gaeumannomyces graminis); powdery mildew of barley (Blumeria graminis), gibberellic disease (fusarium graminearum, fusarium avenaceum, fusarium graminearum, alternaria nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), red rust (Puccinia horneri), yellow rust (barley Puccinia terrestris), loose smut (barley powdery mildew), leaf spot (barley net spot), leaf spot (Cochliobolus graminis), leaf spot (sclerotinia sclerotiorum), leaf spot (rhizoctonia solani), rhizoctonia solani (rhizoctonia solani); rust of corn (maize rust (Puccinia sorghi)), southern rust (Puccinia polyspora), northern leaf spot (septoria turcica)), tropical rust (maize Puccinia zeae), sesame leaf blight (Cochliobolus heterosporus), anthracnose (Colletotrichum graminicola), gray spot (Cercospora zeae-maydis), brown spot (maize hypocrella zeae (Kabatiella zeae)), ascosphaera leaf spot (maize hypocrella zeae), Fusarium graminearum (Fusarium graminearum)), Fusarium nigrospora (maize septoria), sclerotium colorado (maize septoria nigrella), Fusarium graminearum (Fusarium graminearum), Fusarium graminearum (Fusarium graminearum strain); anthracnose of cotton (Colletotrichum gossypii), white mold (Ramularia areola), black spot (Alternaria magna), Alternaria gossypii (Alternaria gossypii))、Root string plantBlack root rot caused by fungi of the genus Thielaviopsis (Thielaviopsis basicola); rust of coffee (camelina rust (Hemileia vastatrix)), leaf spot (Cercospora coffeicola)); sclerotinia sclerotiorum (Sclerotinia sclerotiorum), Alternaria alternata (Alternaria brassica), and root rot disease (Phoma brassicae); rust disease of sugarcane (Puccinia melanothecella, Puccinia cruentesis (Puccinia kuehn)); rust disease of sunflower (Puccinia helionthi), dew fungus disease(Plasmopara halstedii); citrus black spot disease (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum), Penicillium italicum (Penicillium italicum), blight (Phytophthora parasitica), Phytophthora citri (Phytophthora citri) and citrus brown rot (Phytophthora citri); apple blossom blight (sclerotinia mali), apple rot (apple Cladosporium), powdery mildew (Podosphaera leucotricha), Alternaria leaf spot (Alternaria alternata apple pathotype), scab (Venturia nigra), anthracnose (Glomella circinelloidis), Alternaria leaf spot (Diplocarpus mali), ring spot (botrytis cinerea), phytophthora blight (Phytophthora rosea), apple scab (Phanerochaeta), apple scab (Phanerochaete purpurea), ring spot (Phanerochaete chrysosporium), phytophthora blight (Phytophthora infestans), pear scab (Phanerium nipponensis), apple scab (Phanerium roseum), pear scab (Pseudoperonospora japonica), apple scab (Monilinia fructicola), apple scab (Solanum fructicola), apple scab (Monilinia fructicola), apple scab (Gray), apple scab (apple scab), apple scab (Gray), apple scab (apple scab), apple scab (Gray) and apple scab) of pear scab (Gray), apple scab (leaf spot (Gray, apple scab) of pear, apple scab (Gray, apple scab) and apple scab (leaf spot (Gray, apple scab) of the fungus (Gray, apple scab) of pear, apple scab, phoma rot disease (phoma sp.); anthracnose of grapes (Elsinoe ampelina), late blight (Buchner's Cortina), powdery mildew (Uncinula necator), rust (Puccinia ampelina), black rot (Staphylococcus aureus), coccinelliasis (Guignardia bidwellii), and dew bacteria (Vitis vinifera Axis frost-forming fungus)Mold (Plasmopara viticola)); anthracnose of persimmon (Gloeosporium kaki), defoliation (Cercospora kaki), and coccobacillus kaki (mycosphaera nawae); anthracnose of cucurbits (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), gummy stem blight (dimymella bryoniae), brown spot (corynebacterium crenatum), Fusarium oxysporum (Fusarium oxysporum), blight (Pseudoperonospora cubensis), Phytophthora blight (Phytophthora sp.) and seedling blight (Pythium sp.); tomato ring rot (Alternaria solani), leaf mold (Cladosporium fulvum), coal mold (Pseudocercospora furigena), blight (Phytophthora infestans), powdery mildew (levulinella taurica), tomato ring rot (Alternaria solani); brown spot of eggplant (Phomopsis fulva (Phomopsis vexans)), powdery mildew of Compositae (Erysiphe cichororaceae); black spot disease (Alternaria japonica), white spot disease (Cercosporella brassiccus), clubroot disease (Plasmodiophora brassicae), and blight (Peronospora parastica) of cruciferous vegetables; rust disease of welsh onion (Puccinia allii)); soybean purpura (Cercospora kikuchi), anthracnose (Elsinoe glycine), anthracnose (diaphorous phaseolus vulgaris, sojae), rust (Phakopsora pachyrhizi), brown ring rot (corynebacterium sabdaricola), anthracnose (sphacelotheca soja), Colletotrichum gloeosporioides (Colletotrichum gloeosporioides), anthracnose (Colletotrichum gloeosporioides), leaf rot (rhizoctonia solani), brown ring rot (Septoria soja), spot (Cercospora soja), Sclerotinia (sclerotiorum), powdery mildew (soybean powdery mildew), soybean Phytophthora soja (Fusarium solani)), and soybean downy blight (Fusarium solani); sclerotinia and rust of kidney beanFungi (Uromyces apendicularis), angular leaf spot (mucor fusca (phaeosariopsis griseola)), anthracnose (Colletotrichum nodosum)); alternaria alternata (Cercospora personata), Cercospora brown spot (Cercospora arachidicola), sclerotinia sclerotiorum (sclerotinia rolfsii)) of peanuts; powdery mildew of peas (Erysiphe pisi); potato Phytophthora infestans (alternaria solani), Phytophthora infestans (Phytophthora infestans), coccinemia (Phytophthora infestans), pink scab (Spongospora subcontanensis f.sp., subterranean), Verticillium wilt (Verticillium albo-atrum), Verticillium dahliae (Verticillium nigrescens), Verticillium nigrum (Verticillium nigrescens)); powdery mildew of strawberries (Sphaerotheca gracilis (Sphaerotheca humuli)); tea tree netcake disease (Exobasidium reticulatum), alternaria blankii (Elsinoe leucospila), alternaria alternate (Pestalotiopsis sp.), anthracnose (Colletotrichum theae-sinensis)); alternaria longissima (Alternaria longissima), anthracnose (Colletotrichum tabacum), mycosis exposure (Peronospora tabacum), and Phytophthora blight (Phytophthora nicotianae); brown spot of sugar beet (Cercospora betanae (Cercospora betacola)), leaf rot (dermataceae), root rot (dermataceae), black root (Aphanomyces cochlioides), rust (rust of sugar beet (Uromyces betae)); scab of rose (Diplocarpon rosa), powdery mildew (sphacelotheca rosea); brown spot of chrysanthemum (Septoria chrysosporium-indicii), white rust (horiba horizontalis (Puccinia horiana)); white spot blight of onion (Botrytis cinerea), Botrytis cinerea, Botrytis squamosa, Botrytis cinerea), Botrytis cinerea, sclerotinia rot of small bacteria (Botrytis allii), and the like; sclerotinia (sclerotinia) of various crops; alternaria brassicae (Alternaria brassicola); leaf spot of turfgrass (sclerotium homoeocarpa) and grass,Brown and megasphaera (rhizoctonia solani) of turfgrass; and leaf spot of banana (Mycosphaerella filensis, Mycosphaerella xanthophylla, Mycosphaerella musicola).
Seed diseases or diseases in the early growth stage of various crops are caused by a bacterium belonging to the genera Aspergillus (Aspergillus), Penicillium (Penicillium), Fusarium (Fusarium), Gibberella (Gibberella), trichoderma (Tricoderma), Rhizopus (Thielaviopsis), Rhizopus (Rhizopus), Mucor (Mucor), coriolus (coricium), Phoma, Rhizoctonia (Rhizoctonia), and Diplodia (Diplodia). Viral diseases of various crops are mediated by the genera polymyxa (Polymixa) and oleaster (Olpidium).
Seedling blight of rice (Burkholderia plantarii)); gray blight of cucumber (Phytophthora capsici), seedling blight (Pythium ultimum) and spotted bacterial disease (Pseudomonas syringae cucumber var syringae pv. Lachrymans); bacterial wilt of eggplant (Ralstonia solanacearum); citrus canker (Xanthomonas citri)); soft rot of Chinese cabbage (Erwinia carotovora), and the like.
Examples
The present invention will be described more specifically below by showing preparation examples and test examples, but the present invention is not limited to these examples.
First, a preparation example is shown.
Preparation example
[ chemical formula 2]
650mg of the compound represented by the above formula (A) and 223mg of potassium cyanate were added to a mixture of 2.6g of xylene and 1.3g of acetic acid, and stirred at room temperature for 11 hours. To the resulting mixture was added an aqueous sodium hydrogencarbonate solution, the pH of the aqueous layer was adjusted to 6, and then extraction was performed with ethyl acetate. The obtained organic layer was washed with saturated brine and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography to give 342mg of the compound of the present invention.
1H-NMR(CDCl3，23℃)δ(ppm)：7.90-7.89(1H，m)，7.33-7.24(2H，m)，7.18(0.4H，br)，7.09(0.6H，br)，7.01-6.88(2H，m)，5.75(0.4H，br)，4.99-4.84(2H，m)，4.16(2H，q，J=7.0Hz)，3.19-3.00(2H，m)，2.42(0.6H，br)，1.27(3H，q，J=7.0Hz)。
ESI-MS(posi)：522[M＋H]+。
Test examples are shown later.
The non-treated region in test examples 1 to 4 indicates a test region performed under the same conditions as described in each test example except that dimethyl sulfoxide was dispensed instead of a diluted dimethyl sulfoxide solution containing the compound of the present invention.
Test example 1 control test for cucumber Phytophthora gray (Phytophthora capsici)
4.5mg of the compound of the present invention was diluted with 100. mu.L of dimethyl sulfoxide. mu.L of the dilution was dispensed into a titer plate (96 wells), and then 150. mu.L of potato dextrose broth medium (PDB medium) containing zoospores of Phytophthora grisea (Phytophthora capsici) was dispensed. The plate was cultured at 27 ℃ for 3 days to proliferate Phytophthora griseus, and then the absorbance at 600nm of each well of the plate was measured as the growth degree of Phytophthora griseus. Based on the growth degree, the efficacy of the compound of the present invention was 90% or more when the efficacy was calculated using [ formula 1 ].
[ formula 1]
Efficacy of 100X (X-Y)/X
X: degree of growth of bacteria in the treatment-free zone
Y: the extent of growth of bacteria in the treatment area.
Test example 2 control test for Rhizoctonia solani (Pythium ultimum)
4.5mg of the compound of the present invention was diluted with 100. mu.L of dimethyl sulfoxide. mu.L of the dilution was dispensed into a titer plate (96 wells), and then 150. mu.L of Chachi (Czapek) medium containing a hyphal suspension of Rhizoctonia solani (Pythium ultimum) was dispensed. The plate was cultured at 23 ℃ for 5 days to proliferate Rhizoctonia solani, and then the absorbance at 600nm of each well of the plate was measured as the growth degree of Rhizoctonia solani. Based on the growth degree, the efficacy of the compound of the present invention was 90% or more when the efficacy was calculated using [ formula 1 ].
Test example 3 test for controlling Rhizoctonia solani (Pythium ultimum)
1.12mg of the compound of the present invention was diluted with 100. mu.L of dimethyl sulfoxide. mu.L of the dilution was dispensed into a titer plate (96 wells), and then 150. mu.L of Chachi medium containing a hyphal suspension of Rhizoctonia solani (Pythium ultimum) was dispensed. The plate was cultured at 23 ℃ for 5 days to proliferate Rhizoctonia solani, and then the absorbance at 600nm of each well of the plate was measured as the growth degree of Rhizoctonia solani. Based on the growth degree, the efficacy of the compound of the present invention was 90% or more when the efficacy was calculated using [ formula 1 ].
Test example 4 test for controlling barley Cladosporium irregulare (Blastoma tritici)
4.5mg of the compound of the present invention was diluted with 100. mu.L of dimethyl sulfoxide. mu.L of the dilution was dispensed into a titer plate (96 wells), and then 150. mu.L of potato dextrose broth medium (PDB medium) previously inoculated with spores of barley sphaerotheca (Rhizoctonia cerealis). The plate was cultured at 18 ℃ for 7 days to proliferate barley leaf streak bacteria, and then the absorbance at 600nm of each well of the plate was measured as the degree of growth of barley leaf streak bacteria. Based on the growth degree, the efficacy of the compound of the present invention was 90% or more when the efficacy was calculated using [ formula 1 ].
Industrial applicability
The compound of the present invention has a controlling effect on plant diseases and is useful as an active ingredient of a plant disease controlling agent.
Claims (4)
1. A compound represented by the formula (1):
2. a plant disease control agent comprising the compound according to claim 1.
3. A method for controlling plant diseases by treating plants or soil in which plants are cultivated with an effective amount of the compound as described in claim 1.
4. Use of the compound according to claim 1 for controlling plant diseases.
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| WO2021117394A1 (en) * | 2019-12-11 | 2021-06-17 | 住友化学株式会社 | Pyridyloxyacetic acid compound and use of same |
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| CN1148852A (en) * | 1994-05-18 | 1997-04-30 | 拜尔公司 | Substituted diazacyclohexandi (thi) ones |
| EP1095935A1 (en) * | 1999-11-01 | 2001-05-02 | Sumitomo Chemical Company, Limited | 6-Hydroxy-5,6-dihydrouracils as herbicides |
| CN1316426A (en) * | 2000-02-04 | 2001-10-10 | 住友化学工业株式会社 | Uracil compound and its appliance |
| WO2002098227A1 (en) * | 2001-05-31 | 2002-12-12 | Sumitomo Chemical Company, Limited | Plant growth regulators for cotton hervest |
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| EP1736052B1 (en) | 2001-05-31 | 2010-04-21 | Sumitomo Chemical Company, Limited | Stem/leaf desiccant |
| JP2016165426A (en) | 2015-03-10 | 2016-09-15 | 三晃合成工業株式会社 | Liquid suction tool |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1148852A (en) * | 1994-05-18 | 1997-04-30 | 拜尔公司 | Substituted diazacyclohexandi (thi) ones |
| EP1095935A1 (en) * | 1999-11-01 | 2001-05-02 | Sumitomo Chemical Company, Limited | 6-Hydroxy-5,6-dihydrouracils as herbicides |
| CN1316426A (en) * | 2000-02-04 | 2001-10-10 | 住友化学工业株式会社 | Uracil compound and its appliance |
| WO2002098227A1 (en) * | 2001-05-31 | 2002-12-12 | Sumitomo Chemical Company, Limited | Plant growth regulators for cotton hervest |
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